Chicago Family Vacation: What to Do There

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This Christmas season, we decided to leave sunny San Diego behind and take a quick Chicago family vacation. We had a lot of fun bundling up in coats and gloves, and the city had a variety of activities to keep us entertained. I’ve compiled a list of must-dos if you plan to take a family vacation to Chicago.

This wasn’t our first time in Chicago, but it was our first time bringing the kids. We wanted to have a good mix of entertaining the kids, but also some adult items on the itinerary. I think we had a great mix that kept the whole family happy.

Getting From the Airport to Your Hotel

We landed in Chicago at 4:45pm and decided to take the L (their train system) to our hotel. We had about 15 or 16 stops from the airport to the exit closest to our hotel, and it only took about 45 minutes. Had we taken an Uber, it would’ve cost about $50- $60 (we need an Uber XL), but we would’ve been stuck in Friday night rush hour traffic as well. The L system is $5 per person, and kids under 7 are free. You can get on right from the airport, and the blue line takes you into downtown.

Where to Stay During Your Chicago Family Vacation

There are many hotels to choose from in Chicago, and if you stay downtown, you’ll be close to everything. Each time we’ve gone to Chicago, we’ve stayed near the river and have enjoyed some beautiful river views from our hotel room.

We stayed at the Westin Chicago River North because we liked the location of it and because we had Marriott points to use for a free room. Note: If you haven’t started using a travel credit card to help make family travel more affordable, check out my favorite travel cards to get started. What are you waiting for?!

I like the location where we stayed because it was a quick walk over to Millennium Park–which is a great spot for kids and is where you visit The Bean. Another great area to stay in would be the Magnificent Mile area of downtown because there are a lot of shops and restaurants, or closer to Navy Pier, which has a lot to do.

Popular hotels in those areas include:

• Chicago Marriott Downtown Magnificent Mile
• Chicago Hotel Collection Magnificent Mile
• Langham Hotel Chicago
• Hyatt Regency Chicago
• Sheraton Grand Chicago River Walk

Check out my other popular post – The Best Family Hotels in Chicago – for even more great hotel options, along with what is so great about each one.

Deep Dish Pizza – A Must-Do On Your Chicago Family Vacation

Deep dish pizza is a must-do on your Chicago family vacation, and there are many places you can try. Prior to this trip, we had only ever been to Giordano’s Pizza. We loved it so much, we went back each time. But this time we decided to branch out, and we kept hearing great things about the butter crust at Lou Malnati’s.

Maybe it was just because it was our first deep dish experience and it’s stuck with us, but I still think Giordano’s is my favorite. Pizano’s Pizza and Gino’s East are others that have been recommended to us, but we’ll need to catch those on our next trip.

The Navy Pier

The Navy Pier has a little bit of everything. You can find shops and restaurants, the giant sky wheel, dance performances, lake cruises and other seasonal events. There are several small amusement park rides plus fun houses and arcades as well.

Since we were there in December, it was all decorated for Christmas. And we happened to be there the same weekend as the Santa Hustle 5k run, so we decided to participate in that.

Millennium Park & Maggie Daley Park

Millennium Park is where you will find Chicago’s famous Bean. When we were there most recently, it was closed off, but we could still see it from afar. There’s a symphony amphitheater near it, as well as some activities such as ice skating, mini golf and a rock wall.

Just a short walk over to another section of the park, you’ll come to Maggie Daley Park. If you have young kids with you on your Chicago family vacation, this is a great addition to your itinerary. The park area has several playgrounds that are so much fun for the kids. The play structures vary for different ages and all of the kids in our group (ages 4-11) had a blast.

The Game Room

Inside the Chicago Athletic Association Hotel, and just a stone’s throw from Millennial Park, you’ll find The Game Room. When we were done at the park and ready for some food and drinks, this was the perfect spot for us to hit up.

We ordered some appetizers and burgers, a round of shirley temples for the kids, and a bucket of High Noons for us. The kids particularly loved the giant soft pretzel appetizer, while my favorite was the loaded tots. Prices weren’t crazy expensive either, especially for this place being inside of a hotel.

While we enjoyed warming up and having a drink, the kids loved playing shuffleboard, basketball and ski ball. There were also pool tables and lots of TVs to catch whatever sports are on that day. It was a fun vibe, and a good spot to entertain the whole gang.

Nightlife on Your Chicago Family Vacation

Obviously we weren’t trying to hit up any clubs or anything crazy like that when we were in Chicago with kids, but there were still plenty of options to keep us entertained. There are plenty of restaurants you can choose to go to, some with live music as well.

Chicago also has a theater district and when we were there, we had the option of seeing Hamilton or A Christmas Carol.

Overall, we had a blast on our Chicago family vacation, and the kids can’t wait to go back and have some more deep dish pizza. Until next time, Chicago!

Thinking of checking out other big cities with kids? I have resources for things the whole family will love in Seattle, San Francisco, Austin, Kansas City and New Orleans. Plus these are the best family resorts in Virginia.

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